Bruce Robinson had been Johnny Depp's first choice to direct Fear and Loathing in Las Vegas: Robinson was retired from filmmaking at the time, after his bad experiences with the Hollywood system during production on Jennifer 8. The Rum Diary is his first film in nineteen years.
Robinson broke his six-and-a-half year sobriety in order to complete the screenplay, and then again during a particularly stressful moment of shooting. According to Robinson, "Some savage drinking took place. When I was no longer in Johnny's environment I went back to sobriety."